TWI358965B - Electroluminescent devices - Google Patents
Electroluminescent devices Download PDFInfo
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- TWI358965B TWI358965B TW093139854A TW93139854A TWI358965B TW I358965 B TWI358965 B TW I358965B TW 093139854 A TW093139854 A TW 093139854A TW 93139854 A TW93139854 A TW 93139854A TW I358965 B TWI358965 B TW I358965B
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- 239000000463 material Substances 0.000 claims description 120
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 36
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 26
- 239000004305 biphenyl Substances 0.000 claims description 16
- 229910052796 boron Inorganic materials 0.000 claims description 16
- 239000002019 doping agent Substances 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 15
- 235000010290 biphenyl Nutrition 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000002689 soil Substances 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 240000004160 Capsicum annuum Species 0.000 claims 1
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- 125000002015 acyclic group Chemical group 0.000 claims 1
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- 238000000295 emission spectrum Methods 0.000 description 7
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- 238000005481 NMR spectroscopy Methods 0.000 description 3
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- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
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- ZMZSYUSDGRJZNT-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)acetonitrile Chemical compound C1=CC=C2SC(CC#N)=NC2=C1 ZMZSYUSDGRJZNT-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
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- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- AODAEDMAPRQATI-UHFFFAOYSA-N 3-benzylimidazolidine-2,4-dione Chemical compound O=C1CNC(=O)N1CC1=CC=CC=C1 AODAEDMAPRQATI-UHFFFAOYSA-N 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- LTUJKAYZIMMJEP-UHFFFAOYSA-N 9-[4-(4-carbazol-9-yl-2-methylphenyl)-3-methylphenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C(=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C)C(C)=C1 LTUJKAYZIMMJEP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/06—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H—ELECTRICITY
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
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- Chemical & Material Sciences (AREA)
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- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/768,776 US6885026B1 (en) | 2004-01-30 | 2004-01-30 | Organic element for electroluminescent devices |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200526080A TW200526080A (en) | 2005-08-01 |
| TWI358965B true TWI358965B (en) | 2012-02-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093139854A TWI358965B (en) | 2004-01-30 | 2004-12-21 | Electroluminescent devices |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6885026B1 (enExample) |
| JP (1) | JP4965266B2 (enExample) |
| KR (1) | KR101146268B1 (enExample) |
| TW (1) | TWI358965B (enExample) |
| WO (1) | WO2005075600A1 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7329466B2 (en) * | 2004-01-30 | 2008-02-12 | Eastman Kodak Company | Organic element for electroluminescent devices |
| US20060017057A1 (en) * | 2004-07-20 | 2006-01-26 | Cumpston Brian H | Device structure to improve OLED reliability |
| EP2075859B1 (en) * | 2006-10-16 | 2015-03-18 | Toray Industries, Inc. | Light-emitting device |
| US8106199B2 (en) | 2007-02-13 | 2012-01-31 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Organometallic materials for optical emission, optical absorption, and devices including organometallic materials |
| US8278819B2 (en) * | 2007-03-09 | 2012-10-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and display |
| US20080258111A1 (en) * | 2007-04-17 | 2008-10-23 | General Electric Company | Polycarbazolyl(meth)acrylate light emissive compositions |
| US20110301351A1 (en) | 2007-12-21 | 2011-12-08 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Platinum (II) Di (2-Pyrazolyl) Benzene Chloride Analogs and Uses |
| US8389725B2 (en) | 2008-02-29 | 2013-03-05 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Tridentate platinum (II) complexes |
| JP2011526424A (ja) * | 2008-06-26 | 2011-10-06 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機発光ダイオード照明器具 |
| US20100231125A1 (en) * | 2009-03-12 | 2010-09-16 | Sheng Li | Organic light emitting device to emit in near infrared |
| US8206842B2 (en) * | 2009-04-06 | 2012-06-26 | Global Oled Technology Llc | Organic element for electroluminescent devices |
| JP2013502743A (ja) | 2009-08-24 | 2013-01-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機発光ダイオード照明器具 |
| US8716700B2 (en) * | 2009-10-29 | 2014-05-06 | E I Du Pont De Nemours And Company | Organic light-emitting diodes having white light emission |
| US8674343B2 (en) * | 2009-10-29 | 2014-03-18 | E I Du Pont De Nemours And Company | Organic light-emitting diodes having white light emission |
| JP2013509723A (ja) * | 2009-10-29 | 2013-03-14 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機発光ダイオード照明器具 |
| US8716699B2 (en) * | 2009-10-29 | 2014-05-06 | E I Du Pont De Nemours And Company | Organic light-emitting diodes having white light emission |
| US20110266524A1 (en) * | 2009-10-29 | 2011-11-03 | E. I. Du Pont De Nemours And Company | Organic light-emitting diode luminaires |
| WO2015131158A1 (en) | 2014-02-28 | 2015-09-03 | Arizona Board Of Regents On Behalf Of Arizona State University | Chiral metal complexes as emitters for organic polarized electroluminescent devices |
| US9502671B2 (en) | 2014-07-28 | 2016-11-22 | Arizona Board Of Regents On Behalf Of Arizona State University | Tridentate cyclometalated metal complexes with six-membered coordination rings |
| US9818959B2 (en) | 2014-07-29 | 2017-11-14 | Arizona Board of Regents on behlaf of Arizona State University | Metal-assisted delayed fluorescent emitters containing tridentate ligands |
| US9865825B2 (en) | 2014-11-10 | 2018-01-09 | Arizona Board Of Regents On Behalf Of Arizona State University | Emitters based on octahedral metal complexes |
| EP3621970B1 (en) * | 2017-05-11 | 2021-01-13 | Merck Patent GmbH | Organoboron complexes for organic electroluminescent devices |
| JP6903169B2 (ja) | 2017-06-08 | 2021-07-14 | 日東電工株式会社 | ディスプレイデバイスで使用するためのbodipy化合物 |
| CN110729408B (zh) * | 2019-10-23 | 2021-09-28 | 昆山国显光电有限公司 | 一种有机电致发光器件和显示装置 |
| US11778895B2 (en) | 2020-01-13 | 2023-10-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3032546A1 (de) | 1980-08-29 | 1982-05-06 | Basf Ag, 6700 Ludwigshafen | Verfahren zur flaechenmaessigen konzentrierung von licht |
| US4774339A (en) | 1987-08-10 | 1988-09-27 | Molecular Probes, Inc. | Chemically reactive dipyrrometheneboron difluoride dyes |
| DE69624623T2 (de) * | 1995-06-07 | 2003-07-24 | Carnegie Mellon University, Pittsburgh | Versteifte Monomethin-Cyaninfarbstoffe |
| US5683823A (en) | 1996-01-26 | 1997-11-04 | Eastman Kodak Company | White light-emitting organic electroluminescent devices |
| JPH09289081A (ja) | 1996-04-23 | 1997-11-04 | Mitsubishi Chem Corp | 有機電界発光素子 |
| JP3853038B2 (ja) | 1997-09-24 | 2006-12-06 | 三井化学株式会社 | 有機電界発光素子 |
| JP4004712B2 (ja) | 2000-04-12 | 2007-11-07 | 富士フイルム株式会社 | 新規アゾールホウ素化合物、発光素子材料およびそれを使用した発光素子 |
| US6689494B1 (en) * | 2001-09-11 | 2004-02-10 | Bhalchandra M. Karandikar | Light emissive materials for organic light emitting devices (OLED) and OLED based thereupon |
| US6824893B2 (en) * | 2002-02-28 | 2004-11-30 | Eastman Kodak Company | Organic element for electroluminescent devices |
| US6661023B2 (en) * | 2002-02-28 | 2003-12-09 | Eastman Kodak Company | Organic element for electroluminescent devices |
-
2004
- 2004-01-30 US US10/768,776 patent/US6885026B1/en not_active Expired - Lifetime
- 2004-12-21 TW TW093139854A patent/TWI358965B/zh not_active IP Right Cessation
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2005
- 2005-01-18 WO PCT/US2005/002420 patent/WO2005075600A1/en not_active Ceased
- 2005-01-18 KR KR1020067015404A patent/KR101146268B1/ko not_active Expired - Lifetime
- 2005-01-18 JP JP2006551424A patent/JP4965266B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| KR101146268B1 (ko) | 2012-05-16 |
| US6885026B1 (en) | 2005-04-26 |
| JP2007525024A (ja) | 2007-08-30 |
| TW200526080A (en) | 2005-08-01 |
| WO2005075600A1 (en) | 2005-08-18 |
| KR20060133565A (ko) | 2006-12-26 |
| JP4965266B2 (ja) | 2012-07-04 |
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